860 N DENNING DRIVE Winter Park, FL $ 749,900
860 N DENNING DRIVE
$ 749,900
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860 N DENNING DRIVE

Winter Park, FL, 32789
$ 749,900
Bedrooms3 Baths2.1 Sq 1,290

Monthly Estimate*

$ 4,617

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Single Family Home for sale in Winter Park, FL

for $749,900 with 3 bedrooms and 2 full baths, 1 half bath. This 1,290 square foot home was built in 1954 on a lot size of 0.14.

NEW CONSTRUCTION–QUALITY | WALKABLE WINTER PARK | FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional lifestyle. The home features a custom 51’ x 10’ driveway, mature Italian cypress trees, sculptural landscape elements, and elegant iron railing, creating exceptional curb appeal. Covered front and side porches welcome you into a thoughtfully designed interior blending contemporary architecture with refined mid-century influence. Over 300 square feet of newly added living space includes two additional bathrooms, an indoor laundry room, and an oversized primary suite designed as a private retreat. Custom liner windows in the dining room and primary suite provide abundant natural light and architectural character. Interior highlights include: • Tile flooring throughout with custom tile work • Designer kitchen with floating shelves • Smart stove, built-in under-counter microwave and dishwasher • LED under-cabinet and island lighting • Custom light fixtures and ambient lighting throughout • Primary bath with ceiling-mounted rain shower • Zebra blinds throughout • New stacked washer and dryer included The home is fully equipped with modern smart-home technology, including: • New AC system with smart thermostat • Tankless water heater and all-new plumbing • Smart lock entry • Smart soffit exterior lighting • Google doorbell camera and security floodlight cameras with two-way audio • Smart sprinkler system with weather monitoring The private backyard is enclosed with PVC privacy fencing and designed for outdoor living, featuring a porcelain-tiled covered patio and a separate poured slab ideal for a fire pit or grilling area, positioned safely away from the home. Enjoy unmatched proximity to dining, shopping, entertainment, parks, golf, train station, and everyday conveniences including Starbucks, Whole Foods, Publix, restaurants, and movie theater—all just moments away. Homes offering new-construction quality, designer finishes, smart-home integration, and this level of walkability rarely come to market. A turnkey opportunity for the most discerning buyer.

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Single Family Active

Price

$ 749,900

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 4,594

Style

Contemporary Mid-Century Modern

Lot Size

0.14

Year Built

1954

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6370723

Features
General
Sewer Public Sewer
Heating Wall Units / Window Unit
Cooling Wall/Window Unit(s)
Utilities BB/HS Internet Available Cable Available Electricity Connected Fiber Optics Phone Available Public Sewer Connected Sprinkler Meter Street Lights Underground Utilities
Roof Shingle
Appliances Dishwasher Disposal Dryer Ice Maker Microwave Range Range Hood Refrigerator Washer
Zoning R-1A
Patio/Porch Features Covered Deck Front Porch Patio Porch Rear Porch Side Porch
Architectural Style Contemporary Mid-Century Modern
Construction Materials Block Stucco
Year Built 1954
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Subdivision Name MAGNOLIA GARDENS SUB
Facing Direction West
Garage Y/N false
Total Rooms 10
Full Baths 2
Status Active
Directions From Downtown Orlando: Take I-4 East to Exit 87 (Fairbanks Ave). Head east on Fairbanks Ave toward Winter Park. Turn left onto N Denning Drive. Property will be on the right. From Winter Park / Park Avenue: Head west on Fairbanks Ave. Turn right onto N Denning Drive. Property will be on the right. From Lake Mary via Lee Road: Take Lee Road south toward Winter Park. Continue onto Aloma Avenue (FL-426 W) west. Turn left onto N Denning Drive. Property will be on the right.
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 6000
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Lakemont Elem
Land Lease Y/N false
Tax Annual Amount 4594.61
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6370723
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 34
Legal Description MAGNOLIA GARDENS SUB R/85 THE N 20 FT OFLOT 33 & S 40 FT OF LOT 34 BLK B
Minimum Lease 1 Month
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Open Floorplan Primary Bedroom Main Floor Smart Home Thermostat Walk-In Closet(s) Window Treatments
Flooring Porcelain Tile Tile
Furnished Y/N Negotiable
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 1
Laundry Features Electric Dryer Hookup Inside Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Sidewalk
Vegetation Mature Landscaping Trees/Landscaped
Fencing Fenced Other Vinyl Wood
Water Source Public
Lot Size Area 6000
Foundation Details Slab
Building Area Total 1405
Lot Size Acres 0.14
Road Surface Type Concrete
Private Pool false
Waterfront Y/N false
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* Excluded Features
List By
Outlet Realty

Broker

sanderssoldthis@gmail.com

Email

Affordability Calculator

$5,000
Per Month
92%
8%
0%
Monthly Principal & Interest
$4,617
Monthly Property Taxes
$383
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
1/4/2026$749,900 15.39% Price Up
1/4/2026$649,900 Listed Price

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860 N DENNING DRIVE, Winter Park, FL, 32789 is a Single Family Home for sale at $749,900 with 1,290 sqft and a lot size of 0.14. 860 N DENNING DRIVE has 3 bedrooms, 2.1 baths, and was built in 1954. The property's zip code is 32789 which is in Winter Park, FL